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Hydrochloric Acid → 1-(5-Bromothiophen-2-yl)-2-fluoroethan-1-one

HRID 2369037
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HRID 2369037 반응식
[Br:1][C:2]1[S:3][C:4]([C:7](OC)([O:10]C)[CH2:8][F:9])=[CH:5][CH:6]=1.Cl.CCCCCC>CC#N.C(Cl)Cl>[Br:1][C:2]1[S:3][C:4]([C:7](=[O:10])[CH2:8][F:9])=[CH:5][CH:6]=1
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 59632496HCID 59632496, 화합물

생성물 1

HCID 596321641-(5-Bromothiophen-2-yl)-2-fluoroethan-1-one수율 84%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 2-bromo-5-(2-fluoro-1,1-dimethoxy-ethyl)-thiophene (9.4 g, 35 mmol) in MeCN (100 mL) was added 10% aq. HCl (50 mL) at 20° C. and the reaction mixture was stirred at ° C. for 3 h. Solvent was removed in vacuo to afford a residue, which was partitioned between DCM and water, the aqueous layer was extracted with DCM. The combined organic layers were washed with water, sat aq. NaHCO3 and brine, dried over sodium sulfate and evaporated in vacuo to give a white solid. It was dissolved in minimum volume of DCM, and a large volume of hexane was added. After evaporation of most of the solvent, solid precipitated and was then collected with filtration, washed with hexane and dried under high vacuum to afford 1-(5-bromo-thiophen-2-yl)-2-fluoro-ethanone (6.52 g, 84%). 1H-NMR (CDCl3): δ 7.64 (d, 1H), 7.15 (d, 1H), 5.26 (d, 2H).

후처리

  1. customSolvent was removed in vacuo
  2. customto afford a residue, which
  3. customwas partitioned between DCM and water
  4. extractionthe aqueous layer was extracted with DCM
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customto give a white solid
  9. customAfter evaporation of most of the solvent, solid
  10. customprecipitated
  11. filtrationwas then collected with filtration
  12. washwashed with hexane
  13. customdried under high vacuum

출처 및 근거

ORD 기록
ord-b45aa226f40845d28fc0c952760398e2
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08703805B2

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